US6120970A - Polybenzoxazole and polybenzothiazole precursors - Google Patents

Polybenzoxazole and polybenzothiazole precursors Download PDF

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US6120970A
US6120970A US09/161,202 US16120298A US6120970A US 6120970 A US6120970 A US 6120970A US 16120298 A US16120298 A US 16120298A US 6120970 A US6120970 A US 6120970A
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polybenzoxazole
photo
precursor according
polybenzothiazole
precursor
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Recai Sezi
Michael Keitmann
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Polaris Innovations Ltd
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Siemens AG
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/32—Polythiazoles; Polythiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/22—Polybenzoxazoles
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/022—Quinonediazides
    • G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
    • G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides

Definitions

  • the invention relates to novel polybenzoxazole and polybenzothiazole precursors and to resist solutions containing these precursors.
  • thio is used as a convenient abbreviation to denote independently at each occurrence the alternative presence of oxygen or sulfur in hydroxyl, mercaptan, ether and thioether groups, as in poly[phenolcarboxamide phenyl ether] and poly[thiophenolcarboxamide phenyl thioether] precursors for polybenzoxazoles and polybenzothiazoles respectively.
  • polymers are needed as protection and insulation layers.
  • Such polymers can be employed as dielectric between two metal planes, for example in multi chip modules and memory and logic chips, or as buffer coat between the chip and its housing.
  • Some of these polymers for example precursors of aromatic polyimides (PIs) and polybenzoxazoles (PBOs), have good solubility in organic solvents and good film-forming properties and can be applied to the electronic components by inexpensive spin-coating methods.
  • PIs aromatic polyimides
  • PBOs polybenzoxazoles
  • the cyclization is accompanied by disappearance of the polar, hydrophilic groups of the PBO precursor (OH, NH and CO), which would otherwise adversely affect the dielectric properties and water absorption.
  • This is, for example, an essential advantage of polybenzoxazoles over polyimides and in particular over hydroxy-polyimides.
  • the cyclization is not important just for good dielectric properties and low water absorption of the end product, but also for its high heat stability.
  • cyclized end product In contrast to the cyclized end product, they can be applied to a substrate as a soluble precursor and then cyclized, during which the solubility and thus the sensitivity to solvents and other process chemicals decreases greatly. For this reason, the processing of, for example, precyclized polybenzoxazoles is difficult.
  • suitable photoactive components allows the preparation of photo-sensitive compositions, enabling inexpensive, direct structuring of the dielectric.
  • Polybenzoxazoles have the further advantage over polyimides of being structurable in positive mode and developable in aqueous-alkaline media (see EP 0 023 662 B1, EP 0 264 678 B1 and EP 0 291 779 B1).
  • the PBO precursors used must be soluble in alkaline developers, preferably ones which are free from metal ions.
  • BCB Benzocyclobutene
  • a further, important requirement in connection with inexpensive production of microelectronic components is the planarization capacity of the dielectric.
  • the reason for this is that, during the production of such components, level differences occur during application of various layers, making further processing, for example lithographic production of fine structures, more difficult.
  • a planarized substrate allows photo-lithographic processes to be carried out with better dimensional accuracy and greater process tolerances.
  • the use of a dielectric which allows good planarization enables expensive polishing procedures (chemical mechanical polishing, CMP) to be avoided in the production of the components.
  • Alkali-soluble PBO precursors which are suitable for the preparation of photosensitive compositions are disclosed, for example, in EP 0 023 662 B1, EP 0 264 678 B1, EP 0 291 779 B1 and DE 37 16 629 C2; these precursors can be cyclized on the substrate (in this respect, see EP 0 291 778 B1).
  • the known polymers exhibit relatively high moisture absorption, for example 1.7% (see EP 0 291 778 B1), after cyclization (conversion into the polybenzoxazole). There is no mention of the planarization capacity of the polymers prepared.
  • poly [(thio)phenolcarboxamide phenyl(thio)ether] polybenzoxazole and polybenzothiazole precursors which are readily soluble in both organic solvents and in aqueous-alkaline developers which are free from metal ions, are highly suitable for photosensitive compositions and can be processed by spin-coating methods. These precursors are easy to cyclize on substrates and, after cyclization, have, in particular, very low moisture absorption of 1% by weight or even less, and a high degree of planarization, in addition to high heat stability.
  • poly[(thio)phenolcarboxamide phenyl (thio)ether] polybenzoxazole and polybenzothiazole precursors of this invention contain the following partial structure: ##STR3## where: A 1 to A 7 are--independently of one another--H, F, CH 3 , CF 3 , OCH 3 , OCF 3 , CH 2 CH 3 , CF 2 CF 3 , OCH 2 CH 3 or OCF 2 CF 3 ;
  • T is O or S
  • m is 0 or 1
  • the poly[(thio)phenolcarboxamide phenyl (thio)ether] polybenzoxazole or polybenzothiazole precursors of this invention have weight average molecular weights of 1000 to 1,000,000, preferably 5000 to 100000.
  • Polymer precursors of the structure indicated above are prepared by polymerization of one or more corresponding o-aminophenolcarboxylic acids or o-aminothiophenolcarboxylic acids in an organic solvent at a temperature of from 25 to 130° C. in presence of a suitable polymerization reagent.
  • the reagent can be for example triphenyl phosphite used in an equimolar amount.
  • a base such as pyridine and lithium- or calcium chloride can be added to reaction solution (see "Macromolecules" Vol. 18 (1985), pages 616-622).
  • the polymerization can also be carried out in presence of triphenyl phosphine (see DE 37 16 629 C2) or oxalyl chloride.
  • the resulting polymer is then precipitated by adding the reaction solution drop wise to a suitable precipitant.
  • the precipitated polymer is already ready for use after filtration and drying.
  • free amino end groups can be masked, i.e. blocked, using a dicarboxylic anhydride.
  • the poly[(thio)phenolcarboxamide phenyl (thio)ether] polymer precursors of the invention are readily soluble in many organic solvents, such as acetone, cyclohexanone, diethylene glycol monoethyl or diethyl ether, N-methylpyrrblidone, ⁇ -butyrolactone, ethyl lactate, tetrahydrofuran and ethyl acetate, and in aqueous-alkaline developers which are free from metal ions, and can easily be processed by spin-coating methods. After cyclization on the substrate, the resultant polybenzoxazoles and polybenzothiazoles have very low moisture absorption, a high degree of planarization and high heat stability.
  • organic solvents such as acetone, cyclohexanone, diethylene glycol monoethyl or diethyl ether, N-methylpyrrblidone, ⁇ -butyrolactone, ethyl lactate, tetra
  • the poly[(thio)phenolcarboxamide phenyl (thio)ether] precursors of the invention are compatible with diazoketones and are therefore advantageously suitable for photo-resist solutions containing--dissolved in a solvent--a polybenzoxazole or polybenzothiazole precursor and a diazoketone-based photo-active component.
  • photo-active compositions surprisingly exhibit high resolution and very good film quality.
  • the weight ratio between polybenzoxazole or polybenzothiazole precursor and diazoquinone is advantageously between 1:20 and 20:1, preferably between 1:10 and 10:1.
  • the characterizations "A 1 -A 3 " and “A 4 -A 7 " in the structural formulae mean that the aminophenyl groups contain radicals A 1 , A 2 and A 3 , and the carboxyphenyl groups contain radicals A 4 , A 5 , A 6 and A 7 respectively.
  • Particularly suitable solvents for the polymer synthesis are dimethylacetamide, ⁇ -butyrolactone and N-methylpyrrolidone. In principle, however, any solvent in which the starting components are readily soluble can be used.
  • Particularly suitable precipitants are water and mixtures of water with various alcohols, for example ethanol and isopropanol.
  • Cyclization of the o-amino(thio)phenol (thio)ethercarboxylic acid polyamide polybenzoxazole and polybenzothiazole precursors of this invention to moisture- and high temperature stable polybenzoxazoles and polybenothiazoles is effected by heat tempering the precursors at 300-400° C. for 10 minutes to 24 hours, preferably at 325-375° C. for 0.5 to 4 hours.
  • Photo-resist solutions according to this invention are obtained by combining a solution of a o-amino(thio)phenol (thio)ethercarboxylic acid polyamide polybenzoxazole or polybenzothiazole precursor of this invention in an organic solvent with a photoactive diazoketone component and optionally an adhesion promoter.
  • Effective diazoquinones o-benzoquinone and o-naphthoquinone diazides
  • Particularly preferred diazoquinones with these properties include for example N-dehydroabietyl-6-diazo-5(6)-oxo-1-naphthalenesulfonamide, 2,2-bis(4-hydroxyphenylpropane)diester of naphthoquinone [1.2]diazo-(2)-5-sulfonic acid, n-dehydroabietyl-3-diazo-4(3)-oxo-1-naphthalenesulfonamide, N-dehydroabietyl-[5.6.7.8]-tetrahydro-4-diazo-(3(4)-oxo-2-napthalenesulfonamide, and N-dextropimaryl-3-diazo-4-oxo[1.5]-cyclohexadiene-1-sulfonamide.
  • Effective diazoquinones that can be used also include the 1,2-diazonaphthoquinone-4-sulfonic acid and 1,2-diazonapththoquinone-5-sulfonic acid esters of various phenols described in Proc. SPIE 1466 (1991) pages 106-116, which disclosure is here incorporated by reference.
  • Suitable adhesion promoters include, for example, polyamidocarboxylic acids, such as condensation products of an aromatic tetracarboxylic acid dianhydride with a diaminosiloxane.
  • polyamidocarboxylic acids such as condensation products of an aromatic tetracarboxylic acid dianhydride with a diaminosiloxane.
  • Such an adhesion promoter condensation product can have the structure ##STR10##
  • Heat stable and moisture-resistant structures are obtained by coating a photo-resist solution according to this invention on a substrate, exposing to actinic light, electron beam or ion beam through a mask and extracting the solubilized portions resulting from the exposure.
  • Preferred substrates include glass, metal, plastic, or semiconductor material, especially silicon wafers.
  • the clear solution obtained is evaporated in a rotary evaporator until a white solid precipitates.
  • the solid is then stirred in n-hexane, filtered off via a fluted filter and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.
  • the solvent is then removed in a rotary evaporator.
  • the solid residue obtained is washed three times with methanol, filtered off via a Buchner funnel and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.
  • a solution of 20 ml of pyridine in 100 ml of N-methyl-pyrrolidone is then added--in order to complete the reaction--at 0° C., and the mixture is stirred at room temperature for a further 24 hours.
  • the yellow-brown solution is then filtered via a Buchner funnel and added drop wise with vigorous stirring to a mixture of isopropanol and water (1:3).
  • the amount of precipitant isopropanol/water) is selected so that it corresponds to 10 times the reaction solution.
  • the precipitated polymer is filtered off via a Buchner funnel and washed three times with 1% ammonia solution. After purification, the polymer is dried for 72 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.
  • the PBO precursor prepared in this way is readily soluble in solvents such as N-methylpyrrolidone, ⁇ -butyrolactone, acetone, tetrahydrofuran, cyclopentanone, diethylene glycol monoethyl ether, ethyl lactate and ethanol, and in commercially available aqueous-alkaline developers which are free from metal ions, such as NMD-W (Tokyo Ohka).
  • solvents such as N-methylpyrrolidone, ⁇ -butyrolactone, acetone, tetrahydrofuran, cyclopentanone, diethylene glycol monoethyl ether, ethyl lactate and ethanol
  • solvents such as N-methylpyrrolidone, ⁇ -butyrolactone, acetone, tetrahydrofuran, cyclopentanone, diethylene glycol monoethyl ether, ethyl lactate and ethanol
  • NMD-W Tokyo
  • the coated substrate is placed in a tared microbalance (Mettler Toledo AT 261 Deltarange) with a sealed chamber containing phosphorus pentoxide as desiccant.
  • the phosphorus pentoxide is then replaced by a saturated sodium chloride solution, and a relative humidity (23° C.) of 76% is established in the chamber. After storage for a further 24 hours, the weight of the film increases to 0.16424 g. This gives a moisture absorption of 0.63%.
  • An uncoated silicon wafer exhibits no moisture absorption under identical conditions.
  • planarization capacity of polybenzoxazoles prepared from the precursors of the invention by cyclization on a substrate is determined on silicon wafers having aluminum structures 1.2 micron in height (planarization wafers).
  • the degree of planarization is determined as described by D. S. Soane and Z. Martynenko: "Polymers in Microelectronics--Fundamentals and Applications", Elsevier Science Publishers B. V., Amsterdam 1989, pages 189 to 191.
  • the PBO precursor of Example 2 is applied--as in Example 3--to a planarization wafer (substrate) and cyclized.
  • the cyclized film has a thickness of 2.0 micron; the degree of planarization is 75%.
  • Example 3 Some of the cyclized polymer of Example 3 is removed from the substrate after the moisture measurement and analyzed thermogravimetrically (Polymer Laboratories STA 1500 instrument). This analysis shows that a weight loss of 1% is not achieved until a temperature of 490° C. By comparison, a weight loss of 1% is already achieved at a temperature of from 420 to 430° C. in known polybenzoxazoles (see SU 1 205 518 A)
  • a PBO precursor is prepared analogously to Example 2 using--under otherwise identical conditions--4-(4-amino-3-hydroxyphenoxy)-2-(4-carboxyphenoxy)-3,5,6-trifluoro-pyridine (0.1 mol, i.e. 39.2 g) as o-aminophenol-carboxylic acid.
  • the o-aminophenolcarboxylic acid is prepared--analogously to Example 1--from pentafluoropyridine, potassium 4-be nzyloxycarbonylphenoxide and potassium 4-nitro-3-benzyloxyphenoxide.
  • the PBO precursor obtained is readily soluble in the solvents listed in Example 2.
  • a moisture absorption of 0.75% (see Example 3) and a degree of planarization of 77% (see Example 4) are determined.
  • high-temperature-stable resist structures having a resolution of 2 micron at a layer thickness of 1.9 micron are obtained.
  • a PBO precursor is prepared analogously to Example 2 using--under otherwise identical conditions--4-(4-amino-3-hydroxyphenoxy)-2-(4-carboxyphenoxy)-1-trifluoromethyl-3,5,6-trifluorobenzene (0.1 mol, i.e. 45.9 g) as o-aminophenolcarboxylic acid.
  • the o-aminophenolcarboxylic acid is prepared--analogously to Example 1--from octafluorotoluene, potassium 4-benzyloxycarbonylphenoxide and potassium 4-nitro-3-benzyloxyphenoxide.
  • the PBO precursor obtained is readily soluble in the solvents listed in Example 2.
  • a moisture absorption of 0.71% see Example 3
  • a degree of planarization of 82% see Example 4 are determined.
  • high-temperature-stable resist structures having a resolution of 2 micron at a layer thickness of 2.1 micron are obtained.
  • a PBO precursor is prepared analogously to Example 2 using--under otherwise identical conditions--4-(4-amino-3-hydroxy-2,5,6-trifluorophenoxy)benzoic acid (0.1 mol, i.e. 29.9 g) as o-aminophenol-carboxylic acid.
  • the o-aminophenolcarboxylic acid is prepared--via benzyl 4-(4-nitro-3-hydroxy-2,5,6-trifluorophenoxy)benzoate--from pentafluoronitrobenzene and benzyl 4-hydroxy-benzoate (see Example 1).
  • the PBO precursor obtained is readily soluble in the solvents listed in Example 2. From this precursor, a moisture absorption of 0.71% (see Example 3) and a degree of planarization of 83% (see Example 4) are determined. After the photo-structuring carried out as described in Example 6 and cyclization on the substrate, high-temperature-stable resist structures having a resolution of 2 micron at a layer thickness of 2.2 micron are obtained.
  • a PBO precursor is prepared analogously to Example 2 using--under otherwise identical conditions--4-(4-amino-3-hydroxy-2,5,6-trifluorophenoxy)-4'-(4-carboxyphenoxy)-octafluorobiphenyl (0.1 mol, i.e. 61.1 g) as o-aminophenolcarboxylic acid.
  • the o-aminophenolcarboxylic acid is prepared via 4-(4-nitro-3-hydroxy-2,5,6-trifluorophenoxy)-4'-(4-benzyloxycarbonylphenoxy)octafluorobiphenyl (in this respect, see Example 1), which is obtained by reacting 4-(4-benzyloxycarbonylphenoxy)-nonafluorobiphenyl, prepared from decafluorobiphenyl and potassium 4-benzyloxycarbonylphenoxide, with 4-nitrotetra-fluorophenol.
  • the PBO precursor obtained is readily soluble in the solvents listed in Example 2. From this precursor, a moisture absorption of 0.61% (see Example 3) and a degree of planarization of 74% (see Example 4) are determined. After the photo-structuring carried out as described in Example 6 and cyclization on the substrate, high-temperature-stable resist structures having a resolution of 2 micron at a layer thickness of 1.8 micron are obtained.
  • a PBO precursor is prepared analogously to Example 2 using--under otherwise identical conditions--4-(4-amino-3-hydroxy-2,5,6-trifluorophenoxy)-2-(4-carboxyphenoxy)-3,5,6-trifluoropyridine (0.1 mol, i.e. 44.6 g) as o-aminophenolcarboxylic acid.
  • the o-aminophenol-carboxylic acid is prepared via 4-(4-nitro-3-hydroxy-2,5,6-trifluorophenoxy)-2-(4-benzyloxycarbonylphenoxy)-3,5,6-trifluoropyridine (in this respect, see Example 1), which is obtained by reacting 2-(4-benzyloxycarbonyl-phenoxy)-3,4,5,6-tetrafluoropyridine, prepared from pentafluoropyridine and potassium 4-benzyloxycarbonylphenoxide, with 4-nitrotetrafluorophenol.
  • the PBO precursor obtained is readily soluble in the solvents listed in Example 2.
  • a moisture absorption of 0.73% (see Example 3) and a degree of planarization of 75% (see Example 4) are determined.
  • high-temperature-stable resist structures having a resolution of 2 micron at a layer thickness of 2 micron are obtained.

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Cited By (8)

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US20030149207A1 (en) * 2001-07-31 2003-08-07 Andreas Walter Use of polybenzoxazoles (PBOS) for adhesion
US20030176623A1 (en) * 2001-09-28 2003-09-18 Klaus Lowack Poly-o-hydroxyamides, polybenzoxazoles, processes for producing poly-o-hydroxyamides, processes for producing polybenzoxazoles, dielectrics including a polybenzoxazole, electronic components including the dielectrics, and processes for manufacturing the electronic components
SG104255A1 (en) * 1998-09-29 2004-06-21 Sumitomo Bakelite Co Polybenzoxazole resin and precursor thereof
US20040229167A1 (en) * 2003-03-11 2004-11-18 Arch Specialty Chemicals, Inc. Novel photosensitive resin compositions
US20040229160A1 (en) * 2003-03-11 2004-11-18 Arch Specialty Chemicals, Inc. Novel photosensitive resin compositions
US20040249110A1 (en) * 2003-03-11 2004-12-09 Arcr Specialty Chemicals, Inc. Novel photosensitive resin compositions
US20080166659A1 (en) * 2005-02-02 2008-07-10 Byoung-Kee Kim Positive Dry Film Photoresist and Composition For Preparing the Same
US20080305431A1 (en) * 2005-06-03 2008-12-11 Powell David B Pretreatment compositions

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DE10011604A1 (de) 2000-03-10 2001-10-04 Infineon Technologies Ag Polybenzoxazol-Vorstufen
JP4876496B2 (ja) * 2005-02-28 2012-02-15 住友ベークライト株式会社 芳香族化合物およびその誘導体

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DE2647004A1 (de) * 1976-10-18 1978-04-20 Modest Sergejevitsch Akutin Verfahren zur herstellung von polybenzoxazolen
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US20030176623A1 (en) * 2001-09-28 2003-09-18 Klaus Lowack Poly-o-hydroxyamides, polybenzoxazoles, processes for producing poly-o-hydroxyamides, processes for producing polybenzoxazoles, dielectrics including a polybenzoxazole, electronic components including the dielectrics, and processes for manufacturing the electronic components
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US20040249110A1 (en) * 2003-03-11 2004-12-09 Arcr Specialty Chemicals, Inc. Novel photosensitive resin compositions
US20040229167A1 (en) * 2003-03-11 2004-11-18 Arch Specialty Chemicals, Inc. Novel photosensitive resin compositions
US6939659B2 (en) 2003-03-11 2005-09-06 Arch Specialty Chemicals, Inc. Photosensitive resin compositions
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US20080166659A1 (en) * 2005-02-02 2008-07-10 Byoung-Kee Kim Positive Dry Film Photoresist and Composition For Preparing the Same
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EP0905170A2 (fr) 1999-03-31

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